1950s Housewife Stories

6,012 results
Orientation
Length
Source
Infinite Scroll

Pam's Shemale Experience Ch. 08

by majicman21 on Mar 11, 2019
Transgender & Crossdressers

Content warning: one scene with a golden shower... Pam woke with a start. It took her a few seconds to hear her alarm ringing. Next to her, Tanya was still asleep, and further down on the bed, Alex was as well, her head resting on Tanya's thigh. Pam reached over to the bedside table and quickly turned off the alarm. Neither of the other women stirred....

Pam's Shemale Experience Ch. 12

by majicman21 on Oct 12, 2020
Transgender & Crossdressers

Pam and Alex sat together on the bed, the former watching television, the latter on her phone. It was their last night at the hotel. Some of the teachers at the conference had organized a group outing earlier in the night to a nearby restaurant for dinner and drinks, as a farewell of sorts. Pam had gone along, but Tanya had been unable to. "I have a date,...

Old Wife, New Trick

by Boomerpw on Sep 13, 2017
Erotic Couplings

"You're sure you never have?" "Positive." "I mean, not even a little touching when you were a young girl? Or maybe some time when you were half asleep?" "Nope." I was having a difficult time believing that my wife of seventeen years had never masturbated. "You know, I do it all the time." "I guessed as much. But it's different for you--you're a guy." "...

Harriet and The Harlequin Horror

by MeetTheHumpers on Sep 13, 2017
Humor & Satire

H-Cupped Hootered High School Harlot Harriet Humper stars in: "Harriet And The Harlequin Horror" Written by Victor C. Nathan * "Oh, golly, gee whiz, Chuck!" Harriet Humper sighed in a 1950s teenybopper voice of childish seduction, her heavy H-cupped breasts heaving hornily with their nipples erect and pointed as her boyfriend Chuck Dicker slipped his wan...

Twin Exposure Ch. 04

by Decayed Angel on Sep 16, 2017
Novels and Novellas

Chapter 04: Finding Sky Blue and Cloud "You son of a bitch, I ought to kick your ass up and down the parking lot," I shouted at Mike as he climbed out of his car that next morning at work. He immediately ducked back into the car until he saw it was me. "Yeah, you know you deserved it." "Whoa, whoa, what is going on? What did I do?" he asked. "You know wha...

The Midnight Caller

by Monkeyjumper on Sep 17, 2017
BDSM

Although it was a warm evening, the night air felt chill on Sue's naked body. Her heart raced within her chest as she knelt upon an oversized beach blanket in her backyard, but the voice of her master had been most demanding, that she be outside this evening and ready to serve him. Sue thought briefly of the madness of the whole situation, and of the incredi...

Midnight Caller

by Monkeyjumper13 on Sep 13, 2017
BDSM

Although it was a warm evening, the night air felt chill on Sue’s naked body. Her heart raced within her chest as she knelt upon an oversized beach blanket in her backyard, but the voice of her master had been most demanding, that she be outside this evening and ready to serve him. Sue thought briefly of the madness of the whole situation, and of the incredi...

Mistress Diana Ch. 02

by NaughtyWhiteWife on Oct 6, 2020
BDSM

Patty sat on the edge of the cot hoping that if she cooperated with that tall blonde woman then maybe she could find a way to escape this place. She got off the cot, almost losing her balance as she finally grabbed hold of the bars of the cell. The heels were extremely high with platforms plus six inch spikes. Patty held the bars tight trying not to fall as...

Sissy Housewife Learns to Eat Cum

by tiffanyfoxe on Sep 12, 2017
Transsexuals & Crossdressers

Only a few days after Miss Jennifer agreed to let me be her housewife, she informed me that now that I was "pretending to be a girl" and was required to always be dressed completely as a girl, she expected me to service her the way one girl would service another, with my mouth and tongue. At least three times every day (always in the morning before she left...

Hotbeds Ch. 07

by NormaJane on Aug 30, 2017
Erotic Couplings

CHAPTER 7: PLAYING PASSIVE Introduction: The next instalment in the sexual adventures of a prep school teacher in the 1950s and 1960s. ***** I was desolate a good while after the departure of Carmen, not even much interested in having sex, supposing any had been available. There were one or two episodes during the next year, but not worth reporting, as th...